Condominium · City Centre, Mississauga

Chicago Condominiums383 and 385 Prince Of Wales Drive, Mississauga, ON L5B 0C6

Name: Condo Apartment City Centre Real Estate Market Report — 2026-11-01
Creator: The Condo Bar Real Estate
License: https://thecondobar.com/terms

A Master-Planned Residential Tower in Mississauga's City Centre

As of November 2026, Chicago Condominiums has 9 units for sale from $399K to $969K (median $545K) and 4 for rent from $2,250 to $2,800 a month. Maintenance fees run $567 to $780 a month, and these listings have been on the market for an average of 27 days.

Listings updated Nov 4, 1:17 AM EST

Nearby on the map

Rising 32 storeys at 385 Prince of Wales Drive as the sixth tower in The Daniels Corporation's master-planned City Centre, Chicago Condominiums features over 17,000 square feet of lifestyle amenities, including a rock-climbing wall and a virtual golf simulator.

9For Sale

4For Rent

$399K – $969KPrice Range

$2,250 – $2,800/moRent Range

$567–$780Maintenance / mo

27Avg. Days on Market

Year Built: 2010
Units: 417
Floors: 35

9 units for sale at 383 and 385 Prince Of Wales Drive, plus 4 for rent

Current listings at Chicago Condominiums include 2 Condo Townhouses from $700K–$969K and 7 Condo Apartments from $399K–$589K.

9 Units

Nearby

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Listed3 Days Ago

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$399,000

Condo Apartment

385 Prince OF Wales Drive #2809, City Centre, Mississauga

1+1 Beds2 Baths1 Pkg700–799 SqFt

Courtesy of PropTx MLS® / SUTTON GROUP - SUMMIT REALTY INC.
MLS® W14135146

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Listed4 Days Ago

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$589,000

Condo Apartment

385 Prince Of Wales Drive #1611, City Centre, Mississauga

2 Beds2 Baths1 Pkg800–899 SqFt

Courtesy of PropTx MLS® / SAM MCDADI REAL ESTATE INC.
MLS® W14131944

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Listed12 Days Ago

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$459,000

Condo Apartment

385 Prince Of Wales Drive #1802, City Centre, Mississauga

2 Beds1 Baths2 Pkg700–799 SqFt

Courtesy of PropTx MLS® / CENTURY 21 ATRIA REALTY INC.
MLS® W14108204

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Listed14 Days Ago

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$459,000

Condo Apartment

385 Prince Of Wales Drive #317, City Centre, Mississauga

1+1 Beds1 Baths1 Pkg700–799 SqFt

Courtesy of PropTx MLS® / RANEX REALTY GROUP INC.
MLS® W14099846

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Listed20 Days Ago

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$585,000

Condo Apartment

385 Prince Of Wales Drive #1011, City Centre, Mississauga

2 Beds2 Baths1 Pkg800–899 SqFt

Courtesy of PropTx MLS® / EXP REALTY
MLS® W14030648

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Listed29 Days Ago

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$699,999

Condo Townhouse

383 Prince Of Wales Drive #107, City Centre, Mississauga

2+1 Beds3 Baths1 Pkg1,200–1,399 SqFt

Courtesy of PropTx MLS® / HOME AND BUSINESS REALTY
MLS® W13861098

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Listed36 Days Ago

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$545,000

Condo Apartment

385 Prince OF Wales Drive #2304, City Centre, Mississauga

1+1 Beds2 Baths1 Pkg700–799 SqFt

Courtesy of PropTx MLS® / EXP REALTY
MLS® W13837630

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Listed47 Days Ago

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$479,900

Condo Apartment

385 Prince of Wales Drive #3309, City Centre, Mississauga

1+1 Beds2 Baths1 Pkg700–799 SqFt

Courtesy of PropTx MLS® / RE/MAX REALTY ENTERPRISES INC.
MLS® W13799050

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Listed74 Days Ago

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$969,000

Condo Townhouse

383 Prince Of Wales Drive #112, City Centre, Mississauga

3+1 Beds3 Baths2 Pkg1,600–1,799 SqFt

Courtesy of PropTx MLS® / PROPERTY.CA INC.
MLS® W13700790

For BuyersSquare One Condos for SaleNot finding the right fit at Chicago Condominiums? Browse every active listing in the area.Browse Square One Condos for Sale

Same development

Sister Buildings

Part of the same development as Chicago Condominiums, built by The Daniels Corporation.

Chicago Condominiums by address

Chicago Condominiums spans 383 and 385 Prince Of Wales Drive, Mississauga. Here is what is listed at each address right now.

385 Prince Of Wales Drive, Mississauga

For sale:: 7 units, $399K to $589K
For rent:: 4 units, $2,250 to $2,800/mo

383 Prince Of Wales Drive, Mississauga

For sale:: 2 units, $700K to $969K
For rent:: none right now

Keep exploring

There’s more to Chicago Condominiums

01 · InsideIndoor Pool, Concierge and 10 more amenitiesSee inside 02 · The numbersPrices by unit type, fees and recent salesSee the numbers

03 · AboutDetails, who it suits and City CentreRead about it 04 · Schools & nearby8 schools and the places around itSee the area

Amenities

Inside Chicago Condominiums

Building Amenities

Community BBQ
Concierge
Elevator
Exercise Room
Game Room
Gym
Indoor Pool
Media Room
Party Room/Meeting Room
Rooftop Deck/Garden
Sauna
Visitor Parking

Compiled from amenities reported in this building's past listings. Not an official building amenities list and may be incomplete or out of date -- confirm directly with the condo corporation or property management.

The numbers

Chicago Condominiums Market Snapshot

Maintenance fee reflect this building's currently active listings, not an official building-wide figure -- individual units may differ. Data provided by MLS® and should be independently verified; no liability is assumed for any errors or omissions.

Live snapshot of this building's own listings -- rentals not included

Bedrooms

Chicago Condominiums currently has 9 homes for sale, with a median asking price of $545K, averaging 27 days on market. Over the last 24 months, 29 units have sold in the building at a median of $482K — selling at 97% of asking price.

Unit Types in This Building

Unit Type	Listed	Median Asking	Asking Range	Size	Maint. /ft²/mo	Avg. DOM
1 Bed	None listed	—	—	—	—	—
1 Bed + Den	4	$469.5K	$399K–$545K	750 ft²	$0.81–$0.86	25
2 Bed	3	$585K	$459K–$589K	750–850 ft²	$0.90–$0.92	12
2 Bed + Den	1	$700K	$700K	1,300 ft²	$0.44	29
3 Bed	1	$969K	$969K	1,700 ft²	$0.37	74

Prices are current asking prices for active For Sale listings of that unit type -- not sold prices, and not every unit type has one on the market right now. Maint. $/ft²/mo is each type's monthly maintenance fee divided by its size, from this building's current listings only.

Chicago Condominiums by the numbers

vs City Centre and Mississauga

At Chicago Condominiums, the median asking price for condo apartments is $545K, higher than City Centre ($500K) and Mississauga ($525K).

Condo apartments that sold over the last 24 months went for a median of $718 per square foot, higher than City Centre ($650) and Mississauga ($611).

Sales over the last 24 months closed at 97% of the asking price, about the same as City Centre (97%) and Mississauga (97%).

Listings have been on the market for an average of 27 days, shorter than City Centre (51) and Mississauga (55).

There are 7.4 months of inventory at the recent sales pace, more than City Centre (5.6) and Mississauga (6.2).

Metric	Chicago Condominiums Live snapshot · sold last 24mo	City Centre 2026-11-01 · sold last 24mo	Mississauga 2026-11-01 · sold last 24mo
Active Listings	9	251	730
Median Asking Price	$545K	$500K	$525K
Avg. Days on Market	27	51	55
Sold (24mo)	29	1,048	2,730
Median Sold Price	$482K	$505K	$515K
Median $/sqft (Sold)	$718	$650	$611
Sale-to-List Ratio	97%	97%	97%
Months of Inventory	7.4 mo	5.6 mo	6.2 mo

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What buyers and sellers should know about Chicago Condominiums

How Chicago Condominiums compares with City Centre and Mississauga on asking price, time to sell, sold price and how many homes are for sale.

Buyers: do homes here sell above or below asking?
Sellers: how long homes take to sell, here vs nearby
Median sold price and price per square foot
Months of inventory: how long today’s listings would last

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View City Centre Condo Market Report →Mississauga Condo Price Index →

Closed Sales — Last 24 Months

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Buying or selling at Chicago Condominiums? See which way prices are moving

For buyers and sellers: the median sold price per square foot at Chicago Condominiums for each of the last 6 quarters.

Buyers: have prices here been rising or falling?
Sellers: what a square foot has actually sold for, quarter by quarter

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Recently Sold29 soldin the last 24 monthsMedian $482K, 97% of asking. See the address, photos and exact sale price for every recent transaction, free with a registered account.

Aggregate estimates from TRREB MLS® data (PropTx feed). Deemed reliable but not guaranteed, and not an appraisal. Full terms.

The building

About Chicago Condominiums

The community has 417 suites and buildings rising up to 35 storeys, with its most recent building completed in 2010. Amenities include an indoor pool, a concierge, a fitness centre, and a rooftop terrace. Pets are allowed with restrictions.

Master-Planned Urban Living. The Daniels Corporation completed Chicago Condominiums in 2010. It stands at 385 Prince of Wales Drive. It was the sixth tower Daniels built in its downtown master plan, in Mississauga's City Centre. The 32-storey tower has 589 suites.

Generous and Diverse Suite Designs. Suites range from 439 square feet up to 1,276 square feet. The layouts are practical and built for city living.

Exceptional Lifestyle Amenities. Residents have more than 17,000 square feet of amenity space. It includes an indoor pool, a sauna, a fitness centre, a theatre room and a games room. For something different, residents can climb on an indoor wall or practise their swing on a golf simulator.

A Highly Accessible Location. The tower sits in the downtown core, a short walk from Square One. The arts centre, the civic square and the college campus are all nearby. Buses and light rail make it easy to get around without a car, and Highway 403 is a few minutes away.

Nearby and Market. STAK36 and the Limelight towers are close neighbours. For downtown sale trends, see the City Centre report.

City Centre Neighbourhood

Chicago Condominiums is located in City Centre, Mississauga.

See what's nearby -- schools, parks, shopping and transit -- in the map below.

Explore the City Centre neighbourhood guide

The area

Schools & nearby

What’s Nearby

Nearby Schools

Elementary

Corpus Christi School 469 m · 6 min walk
Dufferin-Peel CDSB — JK-8
Fairview Public School 1.0 km · 13 min walk
Peel DSB — JK-6
Huntington Ridge Public School 1.1 km · 14 min walk
Peel DSB — JK-6
St. Giovanni Scalabrini Catholic School 1.2 km · 16 min walk
Dufferin-Peel CDSB — JK-8
St Matthew Separate School 1.3 km · 16 min walk
Dufferin-Peel CDSB — JK-8
Elm Drive (Elementary)1.4 km · 18 min walk
Peel DSB — JK-8
Chris Hadfield P.S. (Elementary)1.7 km · 22 min walk
Peel DSB — JK-5

Secondary

Father Michael Goetz Secondary School 1.3 km · 17 min walk
Dufferin-Peel CDSB — 9-12

All Mississauga schools →

School details come from the Ontario Ministry of Education and the school boards, and may change. Boundaries, programs and grades are set by each board and can change from year to year, so confirm with the board before you buy.

Nearby Amenities

Grocery

Rabba Fine Foods56 m
Food Basics96 m

Park

Community Common239 m
Scholar's Green263 m

Pet Store

The Bone & Biscuit107 m

Point of Interest

mimuseum38 m

Restaurant

The Backyard Smokehouse156 m
Hakka Boyz164 m

Frequently asked questions

Who developed Chicago Condominiums and when was it completed?

Chicago Condominiums was developed by The Daniels Corporation and completed in 2010 as the sixth tower in their master-planned City Centre community.

How many storeys and residential suites are there in the building?

This residential high-rise stands at 32 storeys tall and contains a total of 589 suites.

What are the sizes of the suites at Chicago Condominiums?

Suite floor plans in the building range in size from 439 square feet up to 1,276 square feet.

What recreational amenities can residents enjoy inside the building?

Residents have access to over 17,000 square feet of amenities, including an indoor pool, a sauna, a modern fitness centre, a theatre room, and a games room.

Does Chicago Condominiums feature a rock-climbing wall or virtual golf?

Yes, the building offers unique active recreation options, featuring both a dedicated rock-climbing wall and a virtual golf simulator.

Is Chicago Condominiums located near Square One Shopping Centre?

Yes, the building is situated within Mississauga City Centre, placing residents a short walk away from the shopping, dining, and entertainment options at Square One Shopping Centre.